Ammonium ion binding with pyridine-containing crown ethers

Theresa Chang; Aaron M. Heiss; Stuart J. Cantrill; Matthew C T Fyfe; Anthony R. Pease; Stuart J. Rowan; J. Fraser Stoddart; Andrew J P White; David J. Williams

Ammonium ion binding with pyridine-containing crown ethers

Theresa Chang, Aaron M. Heiss, Stuart J. Cantrill, Matthew C T Fyfe, Anthony R. Pease, Stuart J. Rowan, J. Fraser Stoddart^*, Andrew J P White, David J. Williams

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

48 Citations (Scopus)

Abstract

Dipyrido[24]crown-8 (DP24C8) has been synthesized and shown to form [2]pseudorotaxanes spontaneously with dibenzylammonium ions. These complexes, which have been demonstrated by ¹H NMR spectroscopy to form faster in solution than when the macrocyclic polyether is dibenzo[24]crown-8 (DB24C8), are also stronger than their DB24C8 counterparts. One of the [2]pseudorotaxanes has been used to construct a [2]rotaxane (see above) comprising a dumbbell-shaped component based on a dibenzylammonium ion which is encircled by a DP24C8 macrocycle and terminated by (triphenylphosphonium)methyl stoppers.

Original language	English
Pages (from-to)	2947-2950
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	19
Publication status	Published - 2000 Sept 21
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

Cite this

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title = "Ammonium ion binding with pyridine-containing crown ethers",

abstract = "Dipyrido[24]crown-8 (DP24C8) has been synthesized and shown to form [2]pseudorotaxanes spontaneously with dibenzylammonium ions. These complexes, which have been demonstrated by 1H NMR spectroscopy to form faster in solution than when the macrocyclic polyether is dibenzo[24]crown-8 (DB24C8), are also stronger than their DB24C8 counterparts. One of the [2]pseudorotaxanes has been used to construct a [2]rotaxane (see above) comprising a dumbbell-shaped component based on a dibenzylammonium ion which is encircled by a DP24C8 macrocycle and terminated by (triphenylphosphonium)methyl stoppers.",

author = "Theresa Chang and Heiss, {Aaron M.} and Cantrill, {Stuart J.} and Fyfe, {Matthew C T} and Pease, {Anthony R.} and Rowan, {Stuart J.} and Stoddart, {J. Fraser} and White, {Andrew J P} and Williams, {David J.}",

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language = "English",

volume = "2",

pages = "2947--2950",

journal = "Organic Letters",

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TY - JOUR

T1 - Ammonium ion binding with pyridine-containing crown ethers

AU - Chang, Theresa

AU - Heiss, Aaron M.

AU - Cantrill, Stuart J.

AU - Fyfe, Matthew C T

AU - Pease, Anthony R.

AU - Rowan, Stuart J.

AU - Stoddart, J. Fraser

AU - White, Andrew J P

AU - Williams, David J.

PY - 2000/9/21

Y1 - 2000/9/21

N2 - Dipyrido[24]crown-8 (DP24C8) has been synthesized and shown to form [2]pseudorotaxanes spontaneously with dibenzylammonium ions. These complexes, which have been demonstrated by 1H NMR spectroscopy to form faster in solution than when the macrocyclic polyether is dibenzo[24]crown-8 (DB24C8), are also stronger than their DB24C8 counterparts. One of the [2]pseudorotaxanes has been used to construct a [2]rotaxane (see above) comprising a dumbbell-shaped component based on a dibenzylammonium ion which is encircled by a DP24C8 macrocycle and terminated by (triphenylphosphonium)methyl stoppers.

AB - Dipyrido[24]crown-8 (DP24C8) has been synthesized and shown to form [2]pseudorotaxanes spontaneously with dibenzylammonium ions. These complexes, which have been demonstrated by 1H NMR spectroscopy to form faster in solution than when the macrocyclic polyether is dibenzo[24]crown-8 (DB24C8), are also stronger than their DB24C8 counterparts. One of the [2]pseudorotaxanes has been used to construct a [2]rotaxane (see above) comprising a dumbbell-shaped component based on a dibenzylammonium ion which is encircled by a DP24C8 macrocycle and terminated by (triphenylphosphonium)methyl stoppers.

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M3 - Article

C2 - 10986079

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Ammonium ion binding with pyridine-containing crown ethers

Abstract

ASJC Scopus subject areas

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